Classifications

• • C—CHEMISTRY; METALLURGY
  • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
  • C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G OR C10K; LIQUIFIED PETROLEUM GAS; USE OF ADDITIVES TO FUELS OR FIRES; FIRE-LIGHTERS
  • C10L1/00—Liquid carbonaceous fuels
• • C—CHEMISTRY; METALLURGY
  • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
  • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
  • C09B29/00—Monoazo dyes prepared by diazotising and coupling
  • C09B29/10—Monoazo dyes prepared by diazotising and coupling from coupling components containing hydroxy as the only directing group
  • C09B29/12—Monoazo dyes prepared by diazotising and coupling from coupling components containing hydroxy as the only directing group of the benzene series
• • C—CHEMISTRY; METALLURGY
  • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
  • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
  • C09B29/00—Monoazo dyes prepared by diazotising and coupling
• • C—CHEMISTRY; METALLURGY
  • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
  • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
  • C09B29/00—Monoazo dyes prepared by diazotising and coupling
  • C09B29/24—Monoazo dyes prepared by diazotising and coupling from coupling components containing both hydroxyl and amino directing groups
  • C09B29/26—Amino phenols
• • C—CHEMISTRY; METALLURGY
  • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
  • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
  • C09B31/00—Disazo and polyazo dyes of the type A->B->C, A->B->C->D, or the like, prepared by diazotising and coupling
  • C09B31/02—Disazo dyes
  • C09B31/06—Disazo dyes from a coupling component "C" containing a directive hydroxyl group
  • C09B31/062—Phenols
• • C—CHEMISTRY; METALLURGY
  • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
  • C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G OR C10K; LIQUIFIED PETROLEUM GAS; USE OF ADDITIVES TO FUELS OR FIRES; FIRE-LIGHTERS
  • C10L1/00—Liquid carbonaceous fuels
  • C10L1/003—Marking, e.g. coloration by addition of pigments
• • C—CHEMISTRY; METALLURGY
  • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
  • C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G OR C10K; LIQUIFIED PETROLEUM GAS; USE OF ADDITIVES TO FUELS OR FIRES; FIRE-LIGHTERS
  • C10L1/00—Liquid carbonaceous fuels
  • C10L1/10—Liquid carbonaceous fuels containing additives
  • C10L1/14—Organic compounds
  • C10L1/22—Organic compounds containing nitrogen
  • C10L1/226—Organic compounds containing nitrogen containing at least one nitrogen-to-nitrogen bond, e.g. azo compounds, azides, hydrazines
• • C—CHEMISTRY; METALLURGY
  • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
  • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
  • C10M171/00—Lubricating compositions characterised by purely physical criteria, e.g. containing as base-material, thickener or additive, ingredients which are characterised exclusively by their numerically specified physical properties, i.e. containing ingredients which are physically well-defined but for which the chemical nature is either unspecified or only very vaguely indicated
  • C10M171/007—Coloured or dyes-containing lubricant compositions
• • G—PHYSICS
  • G01—MEASURING; TESTING
  • G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
  • G01N31/00—Investigating or analysing non-biological materials by the use of the chemical methods specified in the subgroup; Apparatus specially adapted for such methods
  • G01N31/22—Investigating or analysing non-biological materials by the use of the chemical methods specified in the subgroup; Apparatus specially adapted for such methods using chemical indicators
• • G—PHYSICS
  • G01—MEASURING; TESTING
  • G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
  • G01N33/00—Investigating or analysing materials by specific methods not covered by groups G01N1/00 - G01N31/00
  • G01N33/26—Oils; Viscous liquids; Paints; Inks
  • G01N33/28—Oils, i.e. hydrocarbon liquids
  • G01N33/2835—Specific substances contained in the oils or fuels
  • G01N33/2882—Markers

Definitions

• the present invention relates to a new method for detection of mineral oils marked with azo dyes and the use thereof of monoazo dyes as markers for mineral oils.
• the object of the present invention was to develop a new method for the detection of mineral oils marked by azo dyes which is easy to implement and by means of which the markers also in a low concentration a strong color reaction can be made visible.
• X 2 , X 3 , X 4 , X 5 and X 6 are, for example, methyl, ethyl, propyl, isopropyl, butyl, isobutyl or sec-butyl.
• Residues X 4 are furthermore, for example, pentyl, isopentyl, neopentyl, tert-pentyl, hexyl, 2-methylpentyl, heptyl, octyl, 2-ethylhexyl or isooctyl.
• R 1 , R 2 , R 3 and R 4 are furthermore, for example, heptyl, octyl, 2-ethylhexyl, isooctyl, nonyl, isononyl, decyl, isodecyl or undecyl (the above terms isooctyl, isononyl and isodecyl are trivial names and derive from the following alcohols obtained in oxosynthesis - cf. Ullmann's Encyclopedia of Industrial Chemistry, 4th edition, volume 7, pages 215 to 217, and volume 11, pages 435 and 436).
• X 4 radicals are furthermore, for example, dimethylamino, diethylamino, dipropylamino, diisopropylamino, dibutylamino, methylamino, ethylamino, propylamino, isopropylamino, butylamino, isobutylamino, sec-butylamino, pentylamino, isopentylamino, neopentylamino, methylpentylamino, methylpentylamino, tert-pentylamino, methylpentylamino Octylamino, 2-ethylhexylamino, isooctylamino, nonylamino, isononylamino, decylamino, isodecylamino, undecylamino, dodecylamino, tridecylamino, 3,5,5,7-tetramethylnonyla
• Residues X 1 are, for example, phenylazo, 2-, 3- or 4-methylphenylazo or 2,4- or 2,6-dimethylphenylazo.
• Residues X 2 , X 4 and X 6 are furthermore, for example, methoxy, ethoxy, propoxy, isopropoxy, butoxy, isobutoxy or sec-butoxy.
• X 2 radicals are furthermore, for example, methoxycarbonyl, ethoxycarbonyl, propoxycarbonyl, isopropoxycarbonyl, butoxycarbonyl, isobutoxycarbonyl, sec-butoxycarbonyl, pentyloxycarbonyl, isopentyloxycarbonyl, neopentyloxycarbonyl, tert-pentyloxycarbonyl, hexyloxycarbonyl, 2-methylpentyloxycarbonyl, octyloxyoxyylyl, heptyloxycarbonyl, octyloxyoxyylyl, heptyloxyoxyoxyylyl, heptyloxycarbonyl, heptyloxycarbonyl, heptyloxycarbonyl, heptyloxycarbonyl, Isononyloxycarbonyl, decyloxycarbonyl, isodecyloxycarbonyl, undecyloxycarbonyl, do
• Suitable alkali or alkaline earth metal hydroxides or alkali carbonates which can be used in the method according to the invention, are e.g. Lithium, sodium, potassium, magnesium or calcium hydroxide or lithium, sodium or potassium carbonate.
• Suitable ammonium compounds of formula II are e.g. Tetramethylammonium hydroxide, Tetraethylammonium hydroxide, tetrapropylammonium hydroxide, Tetrabutylammonium hydroxide, benzyltrimethylammonium hydroxide, Benzyltriethylammonium hydroxide or benzyltributylammonium hydroxide.
• alkali or alkaline earth metal hydroxides as a base is preferred, alkali metal hydroxides being particularly noteworthy.
• Potassium hydroxide as a base, with sodium hydroxide being of particular importance comes to.
• the extractant also contains water, the alkali or alkaline earth metal hydroxides, alkali carbonates or ammonium compounds of formula II, preferably directly as an aqueous solution applied, these usually containing alkali or Alkaline earth hydroxide, alkali carbonate or ammonium compounds of Formula II from 0.1 to 10% by weight, preferably 1 to 10% by weight, each based on the weight of the aqueous solution.
• Suitable solvents are organic solvents which are partially or completely miscible with water. These are, for example, acid amides, in particular carboxamides, such as formamide, N-methylformamide, N, N-dimethylformamide, N, N-diethylformamide, N, N-dimethylacetamide, pyrrolidin-2-one, 1-methylpyrrolidin-2-one (NMP), 1,3-dimethylhexahydropyrimid-2-one or hexamethylphosphonic triamide, N, N, N ', N'-tetramethylguanidine, acetonitrile, nitromethane, amines such as 2-aminoethanol, 1,10-diamino-4,7-dioxadecane, 1.13 -Diamino-4,7,10-trioxatridecane, 2- or 3-methoxypropylamine, 1,8-bis (dimethylamino) naphthalene or an amine of the formula H 2
• Preferred solvents are 1-methylpyrazole, pyrrolidin-2-one, 1-methylpyrrolidin-2-one, dimethyl sulfoxide or sulfolane.
• extractant other additives, e.g. 4-nonylphenol or if 4-nonylphenol is added to the mineral oil before extraction.
• the proportion is based on the weight of the extractant of solvent generally 50 to 99% by weight, preferably 90 up to 99% by weight.
• Aromatic solvents are preferably suitable as solvents Hydrocarbons such as toluene, xylene, dodecylbenzene, diisopropylnaphthalene or a mixture of higher aromatics, which under the The name Shellsol® AB (Shell) is commercially available.
• Shellsol® AB Shellsol® AB
• cosolvents e.g.
• Alcohols such as methanol, ethanol, propanol, isopropanol, Butanol, isobutanol, pentanol, hexanol, heptanol, Octanol, 2-ethylhexanol or cyclohexanol, glycols, such as butylethylene glycol or methyl propylene glycol, amines, such as triethylamine, Diisooctylamine, dicyclohexylamine, aniline, N-methylaniline, N, N-dimethylaniline, Toluidine or xylidine, alkanolamines, such as 3- (2-methoxyethoxy) propylamine, o-cresol, m-cresol, p-cresol, ketones, such as Diethyl ketone or cyclohexanone, lactams, such as ⁇ -butyrolactam, Carbonates, such as ethylene carbonate or propy
• a concentration of azo dye is generally chosen Ia or Ib from 1 to 50 wt .-%, preferably 10 to 50 wt .-%, each based on the solution.
• the azo dye occurs of the formula Ia or Ib in the aqueous phase, which clearly is visibly colored.
• Another object of the present invention is the use of azo dyes of the above formula Ia for marking of mineral oils.
• Mineral oils in the sense of the invention include, for example Fuels such as gasoline, kerosene or diesel oil, or oils such as Heating oil or motor oil.
• the azo dyes of the formula Ia or Ib are particularly suitable for marking mineral oils for which marking is required e.g. for tax reasons. To the cost of The aim is to keep the marking low, for the marking use the smallest possible amount of marker.
• the azo dyes are used to mark mineral oil Formula Ia or Ib, as already stated above, either in Substance or in the form of solutions applied.
• the azo dyes of the formula Ia to be used according to the invention or Ib have the advantage that, depending on their concentration, are suitable for clearly coloring mineral oils and / or can be used as labeling substances.
• Formula Ia or Ib are very easy to use, labeled mineral oils to be detected, even if the labeling substances only exist in one Concentration of about 10 ppm or less.
• the azo dyes of the formula Ia have the Advantage that they have a very good solubility and are also easy to dilute. They can also help with the detection reaction significantly more bathochromic shades can be achieved than with the dyes known from US-A-5 156 653.
• the azo dyes of the formula Ib can be obtained by methods known per se.
• an aniline of formula III in which X 1 , X 2 and X 3 each have the abovementioned meaning diazotize in a conventional manner and the resulting diazonium compound with a phenol of the formula IV in which X 4 , X 5 and X 6 each have the abovementioned meaning, couple.
• the other azo dyes of the formula Ia are in usually about connections known per se. They are e.g. in the US-A-5 156 653 or US-A-4 473 376 can be obtained by the methods mentioned there.
• diesel oil was listed with the following Dyes was marked with different reagent solutions, which are also listed below.
• the dyes F5 and F6 are obtained in an analogous manner.

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• Chemical & Material Sciences (AREA)
• Organic Chemistry (AREA)
• Oil, Petroleum & Natural Gas (AREA)
• Engineering & Computer Science (AREA)
• Chemical Kinetics & Catalysis (AREA)
• General Chemical & Material Sciences (AREA)
• Life Sciences & Earth Sciences (AREA)
• Health & Medical Sciences (AREA)
• Immunology (AREA)
• Pathology (AREA)
• Physics & Mathematics (AREA)
• Analytical Chemistry (AREA)
• Biochemistry (AREA)
• General Health & Medical Sciences (AREA)
• General Physics & Mathematics (AREA)
• Food Science & Technology (AREA)
• Medicinal Chemistry (AREA)
• Biophysics (AREA)
• Molecular Biology (AREA)
• Lubricants (AREA)
• Investigating Or Analyzing Non-Biological Materials By The Use Of Chemical Means (AREA)
• Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
• Paints Or Removers (AREA)
• Cosmetics (AREA)
• Inks, Pencil-Leads, Or Crayons (AREA)
• Investigating Or Analysing Materials By Optical Means (AREA)
• Spectrometry And Color Measurement (AREA)
• Coloring (AREA)
• Developing Agents For Electrophotography (AREA)
• Lubrication Of Internal Combustion Engines (AREA)
• Analysing Materials By The Use Of Radiation (AREA)
• Plural Heterocyclic Compounds (AREA)
• Paper (AREA)

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• 1993
  • 1993-10-12 DE DE4334678A patent/DE4334678A1/de not_active Withdrawn
• 1994
  • 1994-09-29 PH PH49090A patent/PH32006A/en unknown
  • 1994-09-30 FI FI961602A patent/FI961602L/fi unknown
  • 1994-09-30 BR BR9407810A patent/BR9407810A/pt not_active IP Right Cessation
  • 1994-09-30 JP JP7511234A patent/JPH09504314A/ja active Pending
  • 1994-09-30 HU HU9600946A patent/HU217768B/hu not_active IP Right Cessation
  • 1994-09-30 AT AT94928400T patent/ATE180823T1/de not_active IP Right Cessation
  • 1994-09-30 WO PCT/EP1994/003259 patent/WO1995010581A1/de not_active Ceased
  • 1994-09-30 CN CN94194282A patent/CN1046756C/zh not_active Expired - Fee Related
  • 1994-09-30 DE DE59408367T patent/DE59408367D1/de not_active Expired - Lifetime
  • 1994-09-30 KR KR1019960701889A patent/KR100300774B1/ko not_active Expired - Fee Related
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  • 1994-09-30 CA CA002172959A patent/CA2172959A1/en not_active Abandoned
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  • 1994-09-30 DK DK94928400T patent/DK0723574T3/da active
  • 1994-09-30 PL PL94313967A patent/PL313967A1/xx unknown
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  • 1994-10-04 MX MX9407695A patent/MX193901B/es not_active IP Right Cessation
  • 1994-10-05 TW TW83109234A patent/TW291494B/zh active
  • 1994-10-11 ZA ZA947908A patent/ZA947908B/xx unknown
  • 1994-10-12 US US08/321,629 patent/US5487770A/en not_active Expired - Fee Related
• 1996
  • 1996-04-11 NO NO961434A patent/NO961434D0/no not_active Application Discontinuation
• 1999
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